Chemistry:Oxicam
Oxicam is a class of non-steroidal anti-inflammatory drugs (NSAIDs),[1] meaning that they have anti-inflammatory, analgesic, and antipyretic therapeutic effects. Oxicams bind closely to plasma proteins.[2] Most oxicams are unselective inhibitors of the cyclooxygenase (COX) enzymes. The exception is meloxicam with a slight (10:1) preference for COX-2, which, however, is only clinically relevant at low doses.[3]
The most popular drug of the oxicam class is piroxicam.[2] Other examples include: ampiroxicam, droxicam, pivoxicam, tenoxicam, lornoxicam,[2] and meloxicam.
Isoxicam has been suspended as a result of fatal skin reactions.[2]
Chemistry
The physico-chemical characteristics of these molecules vary greatly depending upon the environment.[4]
In contrast to most other NSAIDs, oxicams are not carboxylic acids. They are tautomeric, and can exist as a number of tautomers (keto-enol tautomerism), here exemplified by piroxicam:[1]
Side effects
The use of NSAIDs can, rarely, trigger severe cutaneous adverse reactions such as Stevens–Johnson syndrome (SJS) and toxic epidermal necrolysis (TEN).[5] Epidemiologic studies and reviews have reported that, among NSAIDs, the oxicam derivatives (e.g., piroxicam, tenoxicam, meloxicam) are associated with a comparatively higher risk of SJS/TEN, particularly early after starting treatment, although the absolute risk remains low.[6][7]
Isoxicam was withdrawn/suspended from marketing after reports of fatal skin reactions.[8]
References
- ↑ 1.0 1.1 "Tautomeric transformations of piroxicam in solution: a combined experimental and theoretical study". RSC Advances (England, UK: Royal Society of Chemistry) 5 (40): 31852–31860. March 2015. doi:10.1039/c5ra03653d. Bibcode: 2015RSCAd...531852I.
- ↑ 2.0 2.1 2.2 2.3 "Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents". Clinical Pharmacokinetics 26 (2): 107–20. February 1994. doi:10.2165/00003088-199426020-00004. PMID 8162655.
- ↑ Mutschler, Ernst; Gerd Geisslinger; Heyo K. Kroemer; Monika Schäfer-Korting (2001) (in German). Mutschler Arzneimittelwirkungen: Lehrbuch der Pharmakologie und Toxikologie; mit einführenden Kapiteln in die Anatomie, Physiologie und Pathophysiologie (8 ed.). Stuttgart, Germany: Wissenschaftliche Verlagsgesellschaft. p. 233. ISBN 3-8047-1763-2. OCLC 48723029.
- ↑ "Photophysical studies of oxicam group of NSAIDs: piroxicam, meloxicam and tenoxicam". Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (Elsevier) 59 (6): 1213–22. April 2003. doi:10.1016/S1386-1425(02)00300-1. PMID 12659890. Bibcode: 2003AcSpA..59.1213B.
- ↑ Ward, Kristina E.; Archambault, Raoul; Mersfelder, Tracey L. (2010-02-01). "Severe adverse skin reactions to nonsteroidal antiinflammatory drugs: A review of the literature". American Journal of Health-system Pharmacy: AJHP: Official Journal of the American Society of Health-System Pharmacists 67 (3): 206–213. doi:10.2146/ajhp080603. ISSN 1535-2900. PMID 20101062.
- ↑ Mockenhaupt, Maja; Kelly, Judith Parsells; Kaufman, David; Stern, Robert S.; SCAR Study Group. "The risk of Stevens-Johnson syndrome and toxic epidermal necrolysis associated with nonsteroidal antiinflammatory drugs: a multinational perspective". The Journal of Rheumatology 30 (10): 2234–2240. ISSN 0315-162X. PMID 14528522.
- ↑ Harr, T.; French, L. E. (2010). "Toxic epidermal necrolysis and Stevens-Johnson syndrome". Orphanet Journal of Rare Diseases 5. doi:10.1186/1750-1172-5-39. PMID 21162721.
- ↑ Olkkola, K. T.; Brunetto, A. V.; Mattila, M. J. (1994). "Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents". Clinical Pharmacokinetics 26 (2): 107–120. doi:10.2165/00003088-199426020-00004. PMID 8162655.
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